Dimethylformamide → HCID 86709875, compound

HRID 541051Notes

Reaction equation

[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=[C:4]([C:15]([OH:17])=O)[CH:3]=1.S(Cl)([Cl:20])=O.CN(C)C=O.CN(C1C=CC=CN=1)C>C1(C)C=CC=CC=1.CO>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=[C:4]([C:15]([Cl:20])=[O:17])[CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 4,5-dichloro-6-phenylpicolinic acid (3.00 g, 11.2 mmol) in toluene (40 mL) was added thionyl chloride (1.22 mL, 16.8 mmol) and dimethylformamide (0.04 mL, 0.6 mmol). Reaction mixture was heated at 80° C. for 3 h. HPLC analysis of an aliquot of the reaction mixture treated with methanol and dimethylaminopyridine indicated complete conversion of the starting material. Reaction was allowed to cool to room temperature and concentrated under reduced pressure to provide a white solid. Toluene (40 mL) was added to dissolve the solid and concentrated under reduced pressure and then this process was performed a second time. 4,5-Dichloro-6-phenylpicolinoyl chloride was isolated as a white solid (2.84 g, 89% yield). 1H NMR (400 MHz, CDCl3) δ 8.14 (s, 1H), 7.83-7.75 (m, 2H), 7.55-7.47 (m, 3H); 13C NMR (101 MHz, CDCl3) δ 168.80, 158.88, 146.42, 145.21, 136.79, 134.40, 129.98, 129.61, 128.31, 124.74; MS: Calcd. for C12H6Cl3NO: 284.95. Found: 285 (M+), 250, 222, 187, 152; mp=106-111° C.

Workup

customReaction mixture
customReaction
temperatureto cool to room temperature
concentrationconcentrated under reduced pressure
customto provide a white solid
dissolutionto dissolve the solid
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-da3b9de786144261a9b1c9cb7ca9006a
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871943B2

Reaction notes

Loading…